Water → 1-(Hex-5-en-1-yl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

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Reaction Steps

This example illustrates a synthesis for inventive compound no. 1591 (chemical name and structure above). To a mixture of bromohexene (10.7 g, 66 mmol, available from Aldrich) and sodium hydride (1.58 g, 66 mmol) in dimethylsulfoxide (100 mL) was added theobromine (11.9 g, 66 mmol, available from Sigma). The resulting reaction mixture was stirred for 43 hours. The reaction mixture was treated with water (200 mL) and then extracted with dichloromethane (3×80 mL). The combined extracts were washed with water (3×100 mL), dried over magnesium sulfate, and the solvent subsequently evaporated under vacuum, yielding 17 g of 1-(5-hexenyl)-3,7-dimethylxanthine (65 mmol, 98% yield) as a white powder.

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